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CCATP #676 – Jill McKinley on Windows to Mac Conversion

This week our guest is Jill McKinley, also know as Jill from the North Woods. I’ve been using a Mac since 1984, and other than a 3-year stint using Windows Vista at work, I’ve been heads down in the Mac operating system all that time. Jill has recently bought her first Mac, which as is usually the case turned into a second Mac purchase. She is still straddling both operating systems and honestly not using macOS too much yet. I thought it would be fun to have her come on and chat about what it’s been like to learn macOS and the differences and challenges she’s finding.

If you’d like to chat with Jill, the best place is in the Podfeet Slack. Join us at

mp3 download

Jill wrote a fabulous outline for our conversation but we didn’t get to all of this!


  • I built every computer I had until the Pentium 5 chip and kept them under $300
  • My Apple IIc was expensive, and I was turned off by the Apple rules.
  • I was a Windows support agent, technical lead, and team lead. Learned Windows thoroughly.
  • Kept up always with Apple products out of interest. The cost kept me away. Apple seemed to have one marketing strategy to put them into schools, but students graduated and were too poor to buy any of it. They became Windows users also.
  • Disagreed with decisions like to make everything white, not put CD-ROM drives in because they were ugly. Cater primarily to artists and Hollywood. Aesthetics ruled Apple’s decisions.
  • I started with Windows Phone v1.0 and loved every phone I got from them (HTC). I could swap batteries and install many apps that did amazing things because of the hobbyist programmers. When they created Windows Phone 7.5, it was an OS break, and all software had to be re-written. I did not like the new phones, and they were sunset after version 8. I had to pick between Android and iPhone. I never felt like Android had security, and I avoid all Google products. All the options felt like a step backward from Windows phones.
  • Later got into the iPhone 4s and really liked it. But without the additional batteries and walled garden, I felt limited.
  • Dreamed of a tablet when I worked with them as medical devices. Bought iPad 1 without reviews. It was the device I always dreamed of!
  • I wanted an iPod nano as a watch. As soon as Apple Watch came out, I bought it almost instantly.
  • Bought Allison’s backup MacBook when my work locked down our laptops (smart move). Why not try it from someone I trust.
  • Now have Mac Mini in my recording room for the podcast. I still primarily use my Windows desktop for daily work. I remote into the Mini with Screens and am trying to use it more.

What can I do only in Windows?

  • I play games from Steam, Forza 4, MS Flight Sim, Steam VR. My gaming used to be the primary of what I did on computers. Now I barely have time.
  • CorelDraw for graphics – Could buy the Mac version or something else.
  • Birding apps – Could use it on IOS.
  • Used to need Windows for work, but now everything is only on my work laptop or online, so that is no longer a requirement.
  • A decade ago, I could only do most of my computer activities on Windows, but my computer use changed, and many apps went cross-platform, or I stopped using them.

What can I do only in Mac?

  • Day One
  • IOS Apps
  • Texting on a computer
  • Tight integration with IOS/Apple things
  • Misc. productivity apps like Bear, MindNode, iThoughts, Corkculous, Things3 (now replaced by Todist for me)
  • Feeder4

What can I do only in Both?

  • Capture21 – Raw photo editing
  • Office 365
  • Minecraft
  • Civilization
  • A few Steam games.
  • Tweetdeck
  • Scrivener
  • Logos – Bible software
  • Pocket
  • Slack
  • 1Password

What helps me connect the worlds

  • IFTTT – Smart house control all devices
  • Screen4 – remote desktop
  • Onedrive – All files stored here
  • Synology – All files & photos stored here
  • Smugmug- all photos stored here

Pro’s and Con’s


What do I like about it?

  • I supported it and have used it since version 1 and DOS before it. I can use it easily.
  • Easy for me to get things done. Work is fast for me. Mac is a slog right now.
  • Windows 10 feels intuitive, and everything is just where I would expect it to be.
  • Many free utilities like sound mixing and basic viewers are available.
  • Versatile. I can do almost everything and find a device or app for nearly everything.
  • Low cost – My computers are high spec for around $1000.
  • There are so many brands, form-factors, and specifications from which I can choose from. Pick my own size, chip, graphic card, hard drive, ram, size, shape, features, colors (touch screen, fingerprint, USB C).
  • It’s more flexible screen options and spanning. I can put windows where I want.
  • Customize what is essential to me. I feel like Windows just wants me to do whatever I want.
  • UI and customizations are easy. The Start button and Taskbar are better.
  • I like File Explorer better than Finder (for no good reason)
  • So many ports and accessories are available with different price points. Mostly they are all lower cost than Apple accessories.
  • I still have apps from the 90s that work. I even have a screen saver from my 8088 PC that still works! No hard breaks in OS upgrades that break all software.
  • My daily work on the PC works perfectly well. I am a happy consumer.

What do I dislike?

  • Not moving the ball since Windows 10 came out. It is the best version of Windows ever but primarily unchanged from release. Some of it looks archaic and virtually unchanged since Windows 95. Apps can be ancient too.
  • Feels like the software has more errors. iTunes and iCloud are bizarre on Windows. Not sure who is the blame for that.
  • Used to have more apps in Windows but adding IOS with the M1 chip in changes that.
  • Microsoft abandons hard they try. Zune was better than iPod, but they just ended it. The Surface, which was progressive, is just as costly as a MacBook. I did love my Surface Pro which aged out, but I never was excited enough to buy another. His mostly has to do with power vs. cost.
  • Microsoft tends to abandoned plans for software like OneNote upgrades. Features that were promised for decades never showed up.
  • Never found a backup/restored I liked or that worked perfectly.
  • Random companies, hardware, software, and therefore no consistency in how it all works. Might be inconsistencies between care for the hardware and software. BIOS always different.
  • Developers might just toss software out there to get it done. Feels like you can get something that looks like it was from the 80s or something modern.
  • A lot of finger-pointing in tech about who is the blame for whatever tech help you need. It’s the video card! It’s the bios! It’s HP! It’s the Dell printer.


What do I like about it?

  • Neat productivity apps like Drafts, Bear, Corkulous, Things 3 are available.
  • Programmers take pride in what they produce.
  • IOS apps with M1 in neat but maybe not as awesome as I hoped.
  • Apple’s choices on privacy and security are essential for me. Feels built into the system. Microsoft has to be added to be secure.
  • Losing faith in most corporations, but Apple still impresses me.
  • Apple store, Apple Pay, and auto-updates are better on Mac.
  • AirDrop works ok and is functional.
  • Photos Library is excellent and fun.
  • Safety from hacks, viruses, and tracking is essential. I feel safer on Apple devices.
  • Most of the OS is polished, and there are fewer application errors.
  • Feels like even Office and other cross-platform apps are better on Mac.
  • Apple stands behind its products.
  • The camera always works! I had failures of all sorts with Window’s camera integration on my refi and dr visit. MacBook saved the appointments from failure.
  • You can run Windows in Mac but not the other way around.
  • Unlock everything with an Apple watch.
  • Everything is solidly built. The devices feel like they all have high-quality value.
  • File preview in Finder is nice.
  • Apple makes it easy to do things. But sometimes, ease comes at the cost of choices.
  • Allison makes for a good Apple salesperson. I hear a lot of applications I wish to try.
  • I believe that Apple has come more my way with functionality vs. aesthetics and better prices. I have become more concerned with security and have more money now. With my software needs changing, it feels like we are on a collision course together.

What do I dislike

  • I Don’t know it very well, and without practice, I am not getting better. It’s been a year!
  • I Don’t need it for anything, so there is no draw other than exploration.
  • Costs are high for everything Apple, although there have been some
  • I can’t support it easily when things go wrong. The App store broke for me. I have no idea how to get it how to wake on LAN. Remote access required another app. I was lost in deleting keychains.
  • There are fewer innate abilities than Windows or utilities.
  • Limited options in hardware, specifications are available. Ports seem to be missing on Mac. SD card readers are only on some things.
  • The walled garden and Apple’s choices are sometimes things I disagree with, and there is no recourse. I like how Mac warns you but lets you get apps from other places. I want to see all Apple devices make that same choice. It’s your device. If you’re going to be in the walled garden, stay there but at least let us choose. That will end a lot of controversies. (Fart apps, religious apps, political apps, podcasting apps years ago).
  • It feels like Apple wants to tell us what we want to do and how we want to do it.
  • iCloud is confusing, but I love the settings that sync and apps backup on Apple devices. I feel like the more you are in the Apple world, the easier it gets. iCloud with Windows is baffling.
  • The Windows Registry is baffling, but Terminal activity is beyond me. I hear there is an excellent book on that topic.
  • If you click on an app sometimes, it does not come up. It was explained to me that Mac is document-centric, not software-centric like Windows. It is frustrating sometimes when I don’t understand why my app did not start but instead stays at the dock.
  • The menu on top separated from the app confuses me. If I am lost, 95% of the time, that is the cause. With two screens, it can be even worse.
  • I think Apple sticks to bad decisions for too long. I hear so many frustrated users who waited a long time for specific changes that never happen.
  • UI differences make it slow for me to get things done. Scroll up vs. down, and different keyboard commands make it hard for me to use. It was not quite as intuitive as I always heard it was, or maybe that is a sign of how far Windows 10 improved.

2 thoughts on “CCATP #676 – Jill McKinley on Windows to Mac Conversion

  1. Tim - March 21, 2021

    When Jill mentioned her use of ⇧⌘4 for screen captures you pointed her to the Utility folder where she could find That would have been the perfect time to point out she could use ⇧⌘5 – much quicker method to get to the same place.

  2. Allison Sheridan - March 21, 2021

    I must not have expressed myself well on this, Tim, because you’re the second person to point this out. What I was trying to do was teach Jill that there was a whole pile of goodies in that folder that she might not know about. Thought that would be part of her continuing education of the hidden treasures of macOS. But like I said I must have said it poorly!

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